Winsted, CT 55+ active adult communities & homes for sale

77 communities near Winsted

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Clockmaker's Hill

$100Ks - $100Ks

Clockmaker's Hill, Winsted, CT

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes

3 rating (2 reviews)

Heritage Hills

$300Ks - $900Ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

3.6 rating (7 reviews)

Heritage Village

$100Ks - $500Ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

Rivington

$400Ks - $600Ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

4 rating (1 reviews)

Jefferson Village

$200Ks - $600Ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

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Questions? Call us: (860) 909-8066

Oronoque Village

$200Ks - $600Ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

The Village at Oxford Gre...

$500Ks - $700Ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes

Spring Lake Village

$200Ks - $200Ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

Regency at Prospect

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

The Retreat at Carmel

$400Ks - $600Ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Overlook

$600Ks - $900Ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Meadow Brook Estates

$500Ks - $500Ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

The Summit at Bethel

$600Ks - $600Ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

4.9 rating (14 reviews)

Chatfield Farms

$500Ks - $600Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

Regency at Wappinger

$600Ks - $700Ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

5 rating (1 reviews)

Newtown Woods

$400Ks - $400Ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

Beckley Farms

$300Ks - $400Ks

Beckley Farms, Berlin, CT

New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes

Regency at Fishkill

$400Ks - $500Ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes

South Pond Village

$100Ks - $200Ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

Fieldstone Village

$500Ks - $800Ks

Fieldstone Village, Orange, CT

Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes

North Woods of Colchester

$500Ks - $500Ks

North Woods of Colchester, Colchester, CT

New and Resale | 55+ age-restricted | Built 2007 - present | 140 homes

Fairview at Oxford Greens

$600Ks - $600Ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

3.5 rating (2 reviews)

Harvest Pointe

$800Ks - $3Ms

Harvest Pointe, Cutchogue, NY

New Construction | 55+ age-restricted | Built 2017 - present | 124 homes

Newbury Village

$600Ks - $700Ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

The Gardens of Wilbraham

$500Ks - $500Ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

O'Meara Farm

$400Ks - $500Ks

O'Meara Farm, Farmington, CT

Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes

The Bridges at Oxford Gre...

$600Ks - $600Ks

The Bridges at Oxford Gre..., Oxford, CT

New Construction | 55+ age-restricted | Built 2025 - present | 99 homes

Liberty at Newtown

$300Ks - $400Ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

Applegate Estates

$500Ks - $400Ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

Pond Spring Village

$300Ks - $300Ks

Pond Spring Village, Beacon Falls, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes

Founders Village

$500Ks - $600Ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

Glassbury Court at Cold S...

$500Ks - $700Ks

Glassbury Court at Cold S..., Cold Spring, NY

Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes

Castle Heights of Cheshir...

$500Ks - $600Ks

Castle Heights of Cheshir..., Cheshire, CT

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes

5 rating (1 reviews)

Paris Square

$400Ks - $700Ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Bartlett Hill

$500Ks - $500Ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

Baldwin Station

$400Ks - $400Ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

5 rating (2 reviews)

Benson Woods

$400Ks - $600Ks

Benson Woods, Middlebury, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes

Shaker Heights

$400Ks - $500Ks

Shaker Heights, Enfield, CT

New Construction | 55+ age-restricted | Built 2018 - present | 77 homes

5 rating (3 reviews)

Founders Ridge

$500Ks - $600Ks

Founders Ridge, Middletown, CT

New Construction | 55+ age-restricted | Built 2017 - present | 75 homes

1...2

New The Gardens of Wilbraham

32 LODGE LN # 32, WILBRAHAM, MA, 01095, Wilbraham, MA 01095

$565,000

2 beds

2 baths

1,610 sq ft

Condo

32 LODGE LN # 32, WILBRAHAM, MA, 01095

Community: The Gardens of Wilbraham

The Gardens of Wilbraham

116 CHERRY DR # 116, WILBRAHAM, MA, 0109..., Wilbraham, MA 01095

$539,000

2 beds

2 baths

1,634 sq ft

Condo

116 CHERRY DR # 116, WILBRAHAM, MA, 0109...

11 REVOLUTION RD, COLD SPRING, NY, 10516

Condo

99 MOLLY PITCHER LN B, YORKTOWN HEIGHTS,...

Community: Jefferson Village

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

New Jefferson Village

98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598

$559,900

2 beds

2 baths

1,100 sq ft

Condo

98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,...

Community: Jefferson Village

New Regency at Fishkill

736 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$499,000

1 beds

2 baths

1,543 sq ft

House

736 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Heritage Hills

972 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$575,000

2 beds

2 baths

1,468 sq ft

Condo

972 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

489 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$665,000

2 beds

2 baths

1,483 sq ft

Condo

489 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$675,000

2 beds

2 baths

1,555 sq ft

Condo

141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

Jefferson Village

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598

$569,999

2 beds

2 baths

1,300 sq ft

House

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...

Community: Jefferson Village

Heritage Hills

348 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$600,000

2 beds

2 baths

1,428 sq ft

Condo

348 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Overlook

1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512

$959,000

2 beds

3 baths

2,496 sq ft

Condo

1037 COTTAGE DR 18, CARMEL, NY, 10512

Community: Overlook

Overlook

4057 FAIRWAYS DR # 129, CARMEL, NY, 1051..., Carmel, NY 10512

$699,000

3 beds

4 baths

2,131 sq ft

Condo

4057 FAIRWAYS DR # 129, CARMEL, NY, 1051...

Community: Overlook

Overlook

4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512

$668,000

3 beds

3 baths

1,914 sq ft

Condo

4071 FAIRWAYS DR 136, CARMEL, NY, 10512

Community: Overlook

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Overlook

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512

$665,000

3 beds

3 baths

1,914 sq ft

Condo

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...

Community: Overlook

Jefferson Village

148 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$499,000

2 beds

2 baths

1,159 sq ft

Condo

148 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

Heritage Hills

688 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$725,000

3 beds

2 baths

1,909 sq ft

Condo

688 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

627 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$525,000

1 beds

2 baths

1,098 sq ft

Condo

627 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Heritage Hills

593 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$1,100,000

3 beds

2 baths

1,905 sq ft

Condo

593 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Glassbury Court at Cold Spring

43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516

$729,000

2 beds

3 baths

2,620 sq ft

Condo

43 YESTERDAY DR, COLD SPRING, NY, 10516

Community: Glassbury Court at Cold Spring

Glassbury Court at Cold Spring

5 NORWEGIAN WOOD, COLD SPRING, NY, 10516, Cold Spring, NY 10516

$695,000

2 beds

2 baths

1,974 sq ft

Condo

5 NORWEGIAN WOOD, COLD SPRING, NY, 10516

Community: Glassbury Court at Cold Spring

Heritage Hills

356 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$750,000

2 beds

2 baths

1,435 sq ft

Condo

356 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Regency at Fishkill

326 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$527,000

1 beds

2 baths

1,543 sq ft

Condo

326 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

Harvest Pointe

32 MILLSTONE LN 16, CUTCHOGUE, NY, 11935, Cutchogue, NY 11935

$1,125,000

2 beds

3 baths

1,600 sq ft

Condo

32 MILLSTONE LN 16, CUTCHOGUE, NY, 11935

Community: Harvest Pointe

Want to learn more about 55+ communities in Winsted? 55places can help!

Questions? Call us: (860) 909-8066

Jefferson Village

108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598

$464,900

2 beds

2 baths

1,200 sq ft

Condo

108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ...

Community: Jefferson Village

Heritage Hills

523 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$669,000

2 beds

2 baths

1,468 sq ft

Condo

523 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$375,000

2 beds

2 baths

1,100 sq ft

Condo

45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

Heritage Hills

247 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$389,900

1 beds

1 baths

955 sq ft

Condo

247 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Jefferson Village

2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10..., Yorktown Heights, NY 10598

$299,999

1 beds

1 baths

800 sq ft

Condo

2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10...

Community: Jefferson Village

1 2 3 4…5

Frequently Asked Questions

What size 55+ communities are there in Winsted?

In Winsted, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winsted?

The smallest 55+ community in Winsted has 38 homes, the largest has 38 homes, and the average community consists of 38 homes.

Are there gated 55+ communities in Winsted?

No, there are no gated 55+ communities in Winsted.

Want more information about active adult communities around Winsted?

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77 communities near Winsted

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Winsted, CT 55+ active adult communities & homes for sale

77 communities near Winsted

167 homes near Winsted

2 beds

2 baths

1,610 sq ft

Condo

2 beds

2 baths

1,634 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

3 beds

2 baths

1,793 sq ft

Condo

2 beds

3 baths

1,806 sq ft

Condo

1 beds

2 baths

1,450 sq ft

Condo

2 beds

2 baths

1,427 sq ft

Condo

2 beds

2 baths

1,427 sq ft

Condo

2 beds

2 baths

1,764 sq ft

Condo

2 beds

2 baths

970 sq ft

Condo

2 beds

2 baths

1,555 sq ft

Condo

3 beds

2 baths

1,909 sq ft

Condo

2 beds

2 baths

1,470 sq ft

Condo

2 beds

2 baths

1,159 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

1 beds

2 baths

1,543 sq ft

House

2 beds

2 baths

1,468 sq ft

Condo

2 beds

2 baths

1,483 sq ft

Condo

2 beds